Gabriel Marcotti makes Tottenham narrow favourites to beat Fiorentina.
Spurs were knocked out by the Italian side last time they met, but all three scorers for Fiorentina across the two legs are not at the club any longer, either sold or moved out on loan.
Tottenham have strengthened over the past year, and will not have a League Cup final to play days later as they did later the second leg in Florence last season.
European football expert Gabriel Marcotti has been speaking to Italian outlet Viola News after the draw was made on Monday.
He believes Spurs are a far better side than last year, and picked out Eric Dier as one of the key parts of that.
Asked to pick out Tottenham's weaknesses, he responded: "The two central defenders can be troubled by speed. Kane, who is doing well, sometimes not supported in the best way behind him. Finally this team he lacks experience, it is very young, in a European atmosphere this can be penalised."
Marcotti went on to add that at present he considers Tottenham as narrow favourites to win over two legs, but viewed this as subject to change, warning the intensity of the Premier League could have an effect on how they approach the game.